(2R,3S,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran

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Chemical Name:(2R,3S,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran
CAS No.:842141-75-7
Molecular Formula:C₄₂H₇₂O₆Si₂
Molecular Weight:729.201
Hs Code.:

(2R,3S,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran

Synonyms:(2R,3S,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran

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Chemical Property of (2R,3S,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran

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Technology Process of (2R,3S,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran

There total 11 articles about (2R,3S,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

: 824-94-2
p-methoxybenzyl chloride

: 842141-74-6
(S)-2-Benzyloxy-1-((2R,4S,5S,6R)-5-methyl-4-triisopropylsilanyloxy-6-triisopropylsilanyloxymethyl-tetrahydro-pyran-2-yl)-ethanol

: 842141-75-7
(2R,3S,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride;
DOI:10.1055/s-2004-835661

Reference yield:

: 756834-72-7
(3S,4S)-3-methyl-6-<(tert-butyldimethylsilyl)oxy>-1-hexen-4-ol

: 842141-75-7
(2R,3S,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 11 steps

1: 97 percent / 2,6-lutidine / CH₂Cl₂

2: 48 percent / OsO₄; aq. NMO / tetrahydrofuran

3: 81 percent / p-TsOH; CuSO₄ / 20 °C

4: 80 percent / TPAP; NMO; molecular sieves / CH₂Cl₂

5: 92 percent / 18-crown-6; KHMDS / tetrahydrofuran / -78 °C

6: 99 percent / DIBAL-H / CH₂Cl₂ / -78 °C

7: 67 percent / D-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves

8: 80 percent / NaH; Bu₄NI

9: 52 percent / CSA / CH₂Cl₂; propan-2-ol

10: 91 percent / imidazole / dimethylformamide

11: 71 percent / NaH; Bu₄NI

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; osmium(VIII) oxide; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; 18-crown-6 ether; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; copper(II) sulfate; molecular sieve; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; 5: Horner-Wadsworth-Emmons reaction;
DOI:10.1055/s-2004-835661

Reference yield:

: 842141-55-3
(3S,4S)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-3-triisopropylsilanyloxy-pentanal

: 842141-75-7
(2R,3S,4S,6R)-6-[(S)-2-Benzyloxy-1-(4-methoxy-benzyloxy)-ethyl]-3-methyl-4-triisopropylsilanyloxy-2-triisopropylsilanyloxymethyl-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 7 steps

1: 92 percent / 18-crown-6; KHMDS / tetrahydrofuran / -78 °C

2: 99 percent / DIBAL-H / CH₂Cl₂ / -78 °C

3: 67 percent / D-DET; Ti(O-i-Pr)4; t-BuOOH / molecular sieves

4: 80 percent / NaH; Bu₄NI

5: 52 percent / CSA / CH₂Cl₂; propan-2-ol

6: 91 percent / imidazole / dimethylformamide

7: 71 percent / NaH; Bu₄NI

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; 18-crown-6 ether; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; molecular sieve; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; 1: Horner-Wadsworth-Emmons reaction;
DOI:10.1055/s-2004-835661